American Journal of Innovative Research & Applied Sciences
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| ARTICLES | Am. J. innov. res. appl. sci. Volume 5, Issue 4, Pages 250-253 (October 2017)
American Journal of innovative
Research & Applied Sciences
ISSN 2429-5396 (Online)
OCLC Number: 920041286
| OCTOBER | VOLUME 5 | N° 4 | 2017 |
*Correspondant author and authors Copyright © 2017: | El Houssine Mabrouk 1 | and | Boukallaba Khalid 1 |
1. University Sidi Mohamed Ben Abdellah | Faculty of Sciences Dhar El Mehraz | department of Chemistry | Fez | Morocco |
This article is made freely available as part of this journal's Open Access: ID | Abounada-ManuscriptRef.1-ajira190817 |
SYNTHESIS OF NEW RACEMIC α-TETRAZOLYL α-AMINOESTERS DERIVATIVES, PART II
| El Houssine Mabrouk 1 | and | Boukallaba Khalid 1 |. Am. J. innov. res. appl. sci. 2017; 5(4):250-253.
| PDF FULL TEXT | |Received | 19 August 2017| |Accepted | 16 September 2017| |Published 25 September 2017 |
Background: we report here our results concerning the synthesis of new compounds, as methyl 2-benzamido-2-(5-p-tolyltetrazol-1-yl)acetate and methyl 2-benzamido-2-(5-p-tolyltetrazol-2-yl)acetate, with the aim to have access to new active biomolecules with a good yield through N-alkylation reaction. Objectives: α-Aminoesters possess a broad range of applications ranging from agrochemistry to medicine. We developed a simple, efficient, and environmentally benign method for the Synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters derivatives by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with p-tolyl-1H-tetrazole. The structure of these compounds have been characterized from the rigorous analysis of their spectral 1H-NMR, 13C-NMR and MS. Methods: The N-alkylation reactions of 1H-tetrazole derivative nucleophile with N-benzoylated methyl α-azido glycinate 1 was performed in different solvents (acetone and acetonitrile) for 24 h at room temperature in the presence of various bases (Et3N and DIEPA). Results: The products 2-3 were obtained with an improved overall yields (56.5-63%) by reaction of 1H-tetrazole derivative Nu on azide derivative 1 and were characterized by MS, 1H-NMR and 13C-NMR spectroscopy. Conclusions: we have developed a simple method for the Synthesis of new racemic α-tetrazolyl α-carboxylic aminoesters by nucleophilic substitution of methyl α-azido glycinate N-benzoylated with p-tolyl-1H-tetrazole at room temperature under basic condition using diisopropylethylamine or triethylamine in different solvents (acetone or acetonitrile). The mild reaction conditions, rapid conversion, very satisfactory yields are the notable advantages of the present method.
Keywords: Tetrazole, Nucleophilic substitution, α-Aminoesters, Methyl α-azidoglycinate.